#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/91/7209118.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7209118
loop_
_publ_author_name
'Piecha, Anna'
'Gągor, Anna'
'Jakubas, Ryszard'
'Szklarz, Przemysław'
_publ_section_title
;
 Room-temperature ferroelectricity in diisopropylammonium bromide
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              940
_journal_paper_doi               10.1039/c2ce26580j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C6 H16 Br N'
_chemical_formula_weight         182.11
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.290(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8586(5)
_cell_length_b                   8.0818(5)
_cell_length_c                   7.8918(5)
_cell_measurement_reflns_used    4536
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.88
_cell_volume                     449.38(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4536
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    4.494
_exptl_absorpt_correction_T_max  0.495
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.356(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1533
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0270P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0453
_refine_ls_wR_factor_ref         0.0459
_reflns_number_gt                1270
_reflns_number_total             1533
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26580j.txt
_cod_data_source_block           p21
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7209118
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.35304(4) 0.241081(17) 0.63370(5) 0.04916(12) Uani 1 1 d .
C4 C 0.6142(4) 0.2427(13) 0.2972(4) 0.0479(7) Uani 1 1 d D
C3 C 0.8855(8) 0.1344(10) 0.7037(10) 0.0670(17) Uani 1 1 d .
H3A H 0.7915 0.1119 0.7473 0.101 Uiso 1 1 calc R
H3B H 1.0098 0.1181 0.8055 0.101 Uiso 1 1 calc R
H3C H 0.8677 0.0607 0.6017 0.101 Uiso 1 1 calc R
C1 C 0.8657(7) 0.3117(9) 0.6351(7) 0.0444(14) Uani 1 1 d D
N1 N 0.6705(4) 0.3403(4) 0.4752(4) 0.0384(7) Uani 1 1 d .
H1A H 0.653(5) 0.448(5) 0.439(5) 0.046 Uiso 1 1 d .
H1B H 0.590(5) 0.331(4) 0.520(5) 0.046 Uiso 1 1 d .
C6 C 0.7535(6) 0.2700(12) 0.2170(6) 0.078(2) Uani 1 1 d .
H6A H 0.7155 0.2066 0.1031 0.117 Uiso 1 1 calc R
H6B H 0.8776 0.2355 0.3075 0.117 Uiso 1 1 calc R
H6C H 0.7563 0.3854 0.1892 0.117 Uiso 1 1 calc R
C5 C 0.4163(6) 0.2927(5) 0.1617(6) 0.0650(16) Uani 1 1 d .
H5A H 0.3320 0.2714 0.2175 0.098 Uiso 1 1 calc R
H5B H 0.3763 0.2301 0.0471 0.098 Uiso 1 1 calc R
H5C H 0.4141 0.4085 0.1339 0.098 Uiso 1 1 calc R
C2 C 0.8832(7) 0.4282(6) 0.7940(6) 0.0679(13) Uani 1 1 d .
H2A H 0.8755 0.5407 0.7523 0.102 Uiso 1 1 calc R
H2B H 1.0029 0.4105 0.9020 0.102 Uiso 1 1 calc R
H2C H 0.7820 0.4067 0.8279 0.102 Uiso 1 1 calc R
H1 H 0.9618 0.3314 0.5842 0.081 Uiso 1 1 d RD
H4 H 0.6197 0.1350 0.3289 0.081 Uiso 1 1 d RD
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.05466(18) 0.04247(17) 0.0616(2) -0.0024(5) 0.03600(16) -0.0006(6)
C4 0.0556(18) 0.0422(16) 0.0461(18) 0.003(6) 0.0228(16) -0.001(6)
C3 0.057(3) 0.062(5) 0.070(5) 0.007(4) 0.018(3) 0.004(3)
C1 0.035(2) 0.053(3) 0.039(3) 0.002(2) 0.011(2) -0.0016(18)
N1 0.0397(17) 0.0352(16) 0.045(2) 0.0002(15) 0.0225(16) -0.0015(13)
C6 0.077(2) 0.103(6) 0.075(3) -0.020(4) 0.051(2) -0.002(3)
C5 0.063(2) 0.083(5) 0.044(2) -0.006(2) 0.019(2) -0.011(2)
C2 0.067(3) 0.073(4) 0.054(3) -0.008(3) 0.018(3) 0.000(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 C4 C6 112.2(4)
C5 C4 N1 108.0(5)
C6 C4 N1 110.5(6)
C5 C4 H4 111.4
C6 C4 H4 107.7
N1 C4 H4 106.9
C1 C3 H3A 109.5
C1 C3 H3B 109.5
H3A C3 H3B 109.5
C1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C3 C1 N1 110.4(4)
C3 C1 C2 109.4(6)
N1 C1 C2 106.3(4)
C3 C1 H1 108.3
N1 C1 H1 107.7
C2 C1 H1 114.7
C1 N1 C4 118.1(3)
C1 N1 H1A 112(2)
C4 N1 H1A 105(2)
C1 N1 H1B 108(2)
C4 N1 H1B 112(2)
H1A N1 H1B 100(3)
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C4 C5 1.500(5)
C4 C6 1.504(4)
C4 N1 1.497(7)
C4 H4 0.9017
C3 C1 1.515(7)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C1 N1 1.512(6)
C1 C2 1.525(6)
C1 H1 1.0124
N1 H1A 0.91(4)
N1 H1B 0.85(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.91(4) 2.43(4) 3.335(3) 173(3) 2_656
N1 H1B Br1 0.85(3) 2.51(4) 3.346(3) 168(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 517646
